Synthesis, Biologic Effects, and Biochemical Properties of Some 2’-Azido- and 2’-Amino-2’-Deoxyarabinofuranosyl Pyrimidines and Purines
Various 2’-azido- and 2’-aminoarabinofuranosyl purine and pyrimidine nucleosides have been synthesized. Among these, the derivatives of cytosine and of adenine inhibit the growth of some tumor cell lines in vitro and in vivo. 2’-Azidoarabinofuranosyl cytosine also interferes with the replication of herpes simplex virus types I and II. Whereas 2’-azidoara-C is resistant to deamination by a partially purified CdR deaminase from KB cells, the adenine derivatives are substrates for aminohydrolases partially purified from calf and mouse intestines. Both azido- and aminoara-C are phosphorylated by partially purified CdR kinases from leukemia L1210 and from human AML blast cells. The accumulated data encourage exploration of the clinical utility of the more potent of these analogues.
KeywordsHerpes Simplex Virus Type L1210 Cell Adenosine Deaminase Acute Myelocytic Leukemia Cell Azido Group
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- 5.Cheng YC, Domin B, Lee LS (1977) Human deoxycytidine kinase. Purification and characterization of the cytoplasmic and mitochondrial isozymes derived from blast cells of acute leukemia patients. Biochem Biophys Acta 481:481–492Google Scholar
- 7.Ho DHW, Carter CF, Loo TL (1975) Tetrahydrouridine in the uptake and metabolism of arabinosylcytosine by human acute myelocytic leukemia cells. Proc Am Assoc Cancer Res 16:57Google Scholar
- 9.Ranganathan R, Larwood D (1978) Facile conversion of adenosine into new 2’-substi- tuted-2’-deoxy-arabinofuranosyladenine derivatives: Stereospecific synthesis of 2’-azi- do-2’-deoxy-, 2’-amino-2’-deoxy-, and 2’-mercapto-2’-deoxy-β-D-arabinofuranosylade- nines. Tetrahedron Lett 45:4341–4344CrossRefGoogle Scholar